Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Chester, MD

Search for Condo for Sale in Chester, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 40 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3000 Herons Nest Way #11 CHESTER, MD Love where you live! This highly sought-after first-floor condo is just steps from the wat...	2 beds \| 2 baths \| 2,003 sq.ft.	$498,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.3% Airbnb Rental Income: $null Traditional Rental Income: $2646 Airbnb ROI: N/A Traditional ROI: 1.3%
4000 Herons Nest Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo ...	2 beds \| 2 baths \| 1,900 sq.ft.	$492,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $3311 Airbnb ROI: N/A Traditional ROI: 2.58%
Chester Plan CHESTER, MD Chester Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,319,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.45% Airbnb Rental Income: $null Traditional Rental Income: $1908 Airbnb ROI: N/A Traditional ROI: 0.45%
Magothy Plan CHESTER, MD Magothy Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$1,319,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.48% Airbnb Rental Income: $null Traditional Rental Income: $1931 Airbnb ROI: N/A Traditional ROI: 0.48%
Severn Plan CHESTER, MD Severn Plan, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$1,399,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.52% Airbnb Rental Income: $null Traditional Rental Income: $2155 Airbnb ROI: N/A Traditional ROI: 0.52%
110 Boatswain Way #3042 CHESTER, MD Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a...	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.6% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 0.6%
110 Boatswain Way #42 CHESTER, MD 110 Boatswain Way #42, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $2635 Airbnb ROI: N/A Traditional ROI: 1.81%
2000 Herons Nest Way #401 CHESTER, MD Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at...	3 beds \| 2 baths \| 2,602 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.42% Airbnb Rental Income: $null Traditional Rental Income: $3328 Airbnb ROI: N/A Traditional ROI: 1.42%
111 MARSHGRASS WAY #43 CHESTER, MD Rare opportunity to own a top-floor penthouse offering year-round water views from every r...	2 beds \| 3 baths \| N/A	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.26% Airbnb Rental Income: $null Traditional Rental Income: $3087 Airbnb ROI: N/A Traditional ROI: 1.26%
1000 Herons Nest Way #22 CHESTER, MD BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, season...	2 beds \| 2 baths \| 1,900 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.6% Airbnb Rental Income: $null Traditional Rental Income: $3207 Airbnb ROI: N/A Traditional ROI: 2.6%
132 Wheelhouse Way #11 CHESTER, MD Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot p...	2 beds \| 2 baths \| 2,003 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $3272 Airbnb ROI: N/A Traditional ROI: 2.06%
102 Boatswain Way #2933 CHESTER, MD Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a...	2 beds \| 2 baths \| 1,900 sq.ft.	$809,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $2610 Airbnb ROI: N/A Traditional ROI: 0.28%
102 Boatswain Way #11 CHESTER, MD 102 Boatswain Way #11, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$619,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $2688 Airbnb ROI: N/A Traditional ROI: 2.4%
102 Boatswain Way #2911 CHESTER, MD Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a ...	2 beds \| 2 baths \| 2,003 sq.ft.	$619,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.13% Airbnb Rental Income: $null Traditional Rental Income: $2663 Airbnb ROI: N/A Traditional ROI: 1.13%
114 Merganser Ct CHESTER, MD 114 Merganser Ct, CHESTER, MD 21619 \| Townhouse	2 beds \| 2 baths \| 1,069 sq.ft.	$287,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $1754 Airbnb ROI: N/A Traditional ROI: 1.99%
102 Boatswain Way #33 CHESTER, MD 102 Boatswain Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$809,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.29% Airbnb Rental Income: $null Traditional Rental Income: $2635 Airbnb ROI: N/A Traditional ROI: 1.29%
102 Boatswain Way #32 CHESTER, MD 102 Boatswain Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$809,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.31% Airbnb Rental Income: $null Traditional Rental Income: $2656 Airbnb ROI: N/A Traditional ROI: 1.31%
102 Boatswain Way #43 CHESTER, MD 102 Boatswain Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$909,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.95% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 0.95%
1000 Herons Nest Way #43 CHESTER, MD Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring ...	2 beds \| 2 baths \| 1,832 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $3218 Airbnb ROI: N/A Traditional ROI: 2.52%
830 Warbler Way #21 CHESTER, MD 830 Warbler Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 1.63%
830 Warbler Way #24 CHESTER, MD 830 Warbler Way #24, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 1.63%
830 Warbler Way #34 CHESTER, MD 830 Warbler Way #34, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$849,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.19% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 1.19%
830 Warbler Way #33 CHESTER, MD 830 Warbler Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$689,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $2648 Airbnb ROI: N/A Traditional ROI: 1.89%
830 Warbler Way #43 CHESTER, MD 830 Warbler Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$789,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $2648 Airbnb ROI: N/A Traditional ROI: 1.39%
230 Switchgrass Way #12 CHESTER, MD 230 Switchgrass Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$524,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.14% Airbnb Rental Income: $null Traditional Rental Income: $2434 Airbnb ROI: N/A Traditional ROI: 1.14%
102 Boatswain Way #2943 CHESTER, MD Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a...	2 beds \| 2 baths \| 1,900 sq.ft.	$909,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.07% Airbnb Rental Income: $null Traditional Rental Income: $2648 Airbnb ROI: N/A Traditional ROI: 0.07%
102 Boatswain Way #2932 CHESTER, MD Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a...	2 beds \| 2 baths \| 1,900 sq.ft.	$809,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $3275 Airbnb ROI: N/A Traditional ROI: 1.15%
111 Marshgrass Way #41 CHESTER, MD Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views This...	3 beds \| 2 baths \| 2,602 sq.ft.	$998,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.06% Airbnb Rental Income: $null Traditional Rental Income: $2726 Airbnb ROI: N/A Traditional ROI: -0.06%
201 Switchgrass Way #34 CHESTER, MD 201 Switchgrass Way #34, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$835,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.72% Airbnb Rental Income: $null Traditional Rental Income: $3033 Airbnb ROI: N/A Traditional ROI: 0.72%
110 BOATSWAIN Way #3012 CHESTER, MD Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a ...	2 beds \| 3 baths \| 2,003 sq.ft.	$629,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $3193 Airbnb ROI: N/A Traditional ROI: 3.19%
736 Warbler Way #2733 CHESTER, MD Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-c...	2 beds \| 2 baths \| 1,900 sq.ft.	$719,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $3275 Airbnb ROI: N/A Traditional ROI: 1.6%
736 Warbler Way #33 CHESTER, MD 736 Warbler Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$719,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.68% Airbnb Rental Income: $null Traditional Rental Income: $2622 Airbnb ROI: N/A Traditional ROI: 1.68%
8-F QUEEN VICTORIA WAY CHESTER, MD Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertai...	1 beds \| 1 baths \| N/A	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $1309 Airbnb ROI: N/A Traditional ROI: 2.61%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

3000 Herons Nest Way #11

CHESTER, MD

2 beds | 2 baths | 2,003 sq.ft.

$498,400

Airbnb cash on cash: N/A

Traditional cash on cash: 1.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2646

Airbnb ROI: N/A

Traditional ROI: 1.3%

4000 Herons Nest Way #22

CHESTER, MD

2 beds | 2 baths | 1,900 sq.ft.

$492,500

Airbnb cash on cash: N/A

Traditional cash on cash: 2.58%

Airbnb Rental Income: $null

Traditional Rental Income: $3311

Airbnb ROI: N/A

Traditional ROI: 2.58%

Chester Plan

CHESTER, MD

2 beds | 2 baths | 1,900 sq.ft.

$1,319,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.45%

Airbnb Rental Income: $null

Traditional Rental Income: $1908

Airbnb ROI: N/A

Traditional ROI: 0.45%

Magothy Plan

CHESTER, MD

2 beds | 2 baths | 2,003 sq.ft.

$1,319,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.48%

Airbnb Rental Income: $null

Traditional Rental Income: $1931

Airbnb ROI: N/A

Traditional ROI: 0.48%

Severn Plan

CHESTER, MD

3 beds | 2 baths | 2,602 sq.ft.

$1,399,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2155

Airbnb ROI: N/A

Traditional ROI: 0.52%

110 Boatswain Way #3042

CHESTER, MD

2 beds | 2 baths | 1,900 sq.ft.

$699,990

Airbnb cash on cash: N/A

Traditional cash on cash: 0.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2555

Airbnb ROI: N/A

Traditional ROI: 0.6%

110 Boatswain Way #42

CHESTER, MD

2 beds | 2 baths | 1,900 sq.ft.

$699,990

Airbnb cash on cash: N/A

Traditional cash on cash: 1.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2635

Airbnb ROI: N/A

Traditional ROI: 1.81%

2000 Herons Nest Way #401

CHESTER, MD

3 beds | 2 baths | 2,602 sq.ft.

$700,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.42%

Airbnb Rental Income: $null

Traditional Rental Income: $3328

Airbnb ROI: N/A